Epoxidations with m-chloroperoxybenzoic acid

Camphanyl ester 3 was epoxidized with m-chloroperoxybenzoic acid and the two stereoisomeric epoxides [of the lyxo 7 and ribo 8 configurations, (1 1.1,90%)] were separated by column chromatography with light petroleum-ethyl acetate (65 35). The ribo-epoxide 8 was hydrolyzed with 1 N HC104 in dioxane-water solution to methyl 4-deoxy-D-xylo-hexopyranoside, identified as the 2,3,6-tri-O-acetyI derivative 9 mp 74°C, [ot]589 + 139.1° (c 0.56, CHC13) reported [49] mp 75°-76°C, [a]589 + 138° (CHCI3). 

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